Synthesis and Characterization of Biphenylene-Containing Diazaacenes

被引：32

作者：

Biegger, Philipp ^{[1
]}

Schaffroth, Manuel ^{[1
]}

Patze, Christian ^{[1
]}

Tverskoy, Olena ^{[1
]}

Rominger, Frank ^{[1
]}

Bunz, Uwe H. F. ^{[1
,2
]}

机构：

[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany

[2] Heidelberg Univ, Ctr Adv Mat, D-69120 Heidelberg, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 19期

关键词：

aromaticity; condensation; cyclobutadiene; diazaacene; CHEMICAL-SHIFTS NICS; AROMATICITY;

D O I：

10.1002/chem.201500319

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe the efficient synthesis of substituted benzo[3,4]cyclobuta[1,2-b]phenazine, benzo[3,4]cyclobuta[1,2]benzo[1,2-i]phenazine, and benzo[3,4]cyclobuta[1,2-b]naphtho[2,3-i]phenazine by a condensation reaction of aromatic diamines with the stable biphenylene-2,3-dione.

引用

页码：7048 / 7052

页数：5

共 32 条

[1] Oxyfunctionalization of biphenylene by singlet oxygen, hydrogen peroxide/methyltrioxorhenium, and dimethyldioxirane [J].

Adam, W ;

Balci, M ;

Kilic, H .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8544-8546

[2] Effects of electronegative substitution on the optical and electronic properties of acenes and diazaacenes [J].

Appleton, Anthony Lucas ;

Brombosz, Scott M. ;

Barlow, Stephen ;

Sears, John S. ;

Bredas, Jean-Luc ;

Marder, Seth R. ;

Bunz, Uwe H. F. .

NATURE COMMUNICATIONS, 2010, 1

[3] Soluble Diazaiptycenes: Materials for Solution-Processed Organic Electronics [J].

Biegger, Philipp ;

Stolz, Sebastian ;

Intorp, Sebastian N. ;

Zhang, Yexiang ;

Engelhart, Jens U. ;

Rominger, Frank ;

Hardcastle, Kenneth I. ;

Lemmer, Uli ;

Qian, Xuhong ;

Hamburger, Manuel ;

Bunz, U. H. F. .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01) :582-589

[4] BIPHENYLENES .8. SYNTHESIS AND REACTIONS OF 2-HYDROXYBIPHENYLENE AND OF BIPHENYLENE-2,3-QUINONE [J].

BLATCHLY, JM ;

THATTE, SD ;

MCOMIE, JFW .

JOURNAL OF THE CHEMICAL SOCIETY, 1962, (DEC) :5090-&

[5] Alkynylated Phenazines: Synthesis, Characterization, and Metal-Binding Properties of Their Bis-Triazolyl Cycloadducts [J].

Bryant, Jonathan J. ;

Zhang, Yexiang ;

Lindner, Benjamin D. ;

Davey, Evan A. ;

Appleton, Anthony Lucas ;

Qian, Xuhong ;

Bunz, U. H. F. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17) :7479-7486

[6]

Bunz U. H. F., 2013, ANGEW CHEM, V125, P3898

[7] Large N-Heteroacenes: New Tricks for Very Old Dogs? [J].

Bunz, Uwe H. F. ;

Engelhart, Jens U. ;

Lindner, Benjamin D. ;

Schaffroth, Manuel .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) :3810-3821

[8] The larger N-heteroacenes [J].

Bunz, Uwe H. F. .

PURE AND APPLIED CHEMISTRY, 2010, 82 (04) :953-968

[9] N-Heteroacenes [J].

Bunz, Uwe H. F. .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (28) :6780-6789

[10] Electrochemical Considerations for Determining Absolute Frontier Orbital Energy Levels of Conjugated Polymers for Solar Cell Applications [J].

Cardona, Claudia M. ;

Li, Wei ;

Kaifer, Angel E. ;

Stockdale, David ;

Bazan, Guillermo C. .

ADVANCED MATERIALS, 2011, 23 (20) :2367-2371

← 1 2 3 4 →